HCID 86754917, compound → Cefadroxil monohydrate

HRID 2198557Notes

Reaction equation

HRID 2198557 reaction equation
[CH3:1][C:2]1[CH2:22][S:21][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:20])[C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:23]([OH:25])=[O:24].CN(C=[O:30])C>CN(C=O)C>[CH3:1][C:2]1[CH2:22][S:21][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:20])[C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:23]([OH:25])=[O:24].[OH2:30]

Participants

3

Reactant 1

HCID 86754917HCID 86754917, compound

Product 1

HCID 47964Cefadroxil monohydrateYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

400 ml of dichloromethane and 45.3 ml (327 mmol) of triethylamine were added to 35.0 g of 7-ADCA (163 mmol) and 41.5 ml (327 mmol) of trimethylchlorosilane were added dropwise over a few minutes without cooling while the temperature raised to 38° C. After refluxing for one hour at 38° to 40° C. the reaction mixture was cooled to -30° C. and then 82.2 g of cefadroxil-DMF solvate were obtained by following the same additional steps B and C of Example 3 for a yield of 98.8%. The structure was confirmed by IR and PMR spectra, indicating a high purity of the obtained product. Using the same process of Step D of Example 3, the cefadroxil-DMF solvate was converted into 41.5 g of cefadroxil-monohydrate. The structure was confirmed by IR and PMR spectra which indicated a high purity of the said product. According to a Karl Fisher test, the moisture content seemed to be 5.5%. From the mother liquor, an additional 23 g of DMF solvate could be obtained for an overall yield of 89.5% of cefadroxil monohydrate based on the starting 7-ADCA.

Sources & evidence

ORD record
ord-1bff317426fe414c9696185021f01801
Source dataset
uspto-grants-1982_11
Patent number
US04358588

Reaction notes

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